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Rizzo with signature.pdf (2.33 MB)
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Synthesis of Bis(2,2,2-Trifluoroethyl) (Z)-Vinylphosphonates
Author Info
Rizzo, Lee A.
Permalink:
http://rave.ohiolink.edu/etdc/view?acc_num=ysu1380022849
Abstract Details
Year and Degree
2013, Master of Science in Chemistry, Youngstown State University, Department of Chemistry.
Abstract
A new method for the synthesis of bis (2,2,2- trifluoroethyl) (Z)-vinyl phosphonates from bis (2,2,2-trifluoroethyl) 1-alkynyl phosphonates is described. 1-Alkynyl phosphonates, in the presence of Lindlar's catalyst, trifluoroethanol and H
2
(g), are used to prepare the corresponding vinylphosphonates via a semireductive synthetic approach. With the starting materials in hand, specifically the 1-alkynylphophonates, which were synthesized using bis(2,2,2-trifluoroethyl)phosphorochloridate and the commercially available 1-alkynes, the obtaining of the desired target was accomplished. The semireduction of the triple bond was successful using Lindlar's catalyst in the presence of quinoline with 2,2,2-trifluoroethanol as reaction solvent. Additionally, a modified approach to this synthesis is explored such that only the kinetic (
Z
) isomer is formed.
Committee
John Jackson, Ph.D. (Advisor)
Peter Norris, Ph.D. (Committee Member)
Timothy Wagner, Ph.D. (Committee Member)
Pages
93 p.
Subject Headings
Agricultural Chemicals
;
Chemistry
;
Organic Chemistry
;
Pharmaceuticals
Keywords
vinyl phosphonates
;
hydrogenation
;
semi-reduction
;
lindlar catalyst
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Citations
Rizzo, L. A. (2013).
Synthesis of Bis(2,2,2-Trifluoroethyl) (Z)-Vinylphosphonates
[Master's thesis, Youngstown State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ysu1380022849
APA Style (7th edition)
Rizzo, Lee.
Synthesis of Bis(2,2,2-Trifluoroethyl) (Z)-Vinylphosphonates.
2013. Youngstown State University, Master's thesis.
OhioLINK Electronic Theses and Dissertations Center
, http://rave.ohiolink.edu/etdc/view?acc_num=ysu1380022849.
MLA Style (8th edition)
Rizzo, Lee. "Synthesis of Bis(2,2,2-Trifluoroethyl) (Z)-Vinylphosphonates." Master's thesis, Youngstown State University, 2013. http://rave.ohiolink.edu/etdc/view?acc_num=ysu1380022849
Chicago Manual of Style (17th edition)
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Document number:
ysu1380022849
Download Count:
844
Copyright Info
© 2013, all rights reserved.
This open access ETD is published by Youngstown State University and OhioLINK.